(Diethylamino)sulfur trifluoride → (rac)-7-fluoro-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one

HRID 2046186Notes

Reaction equation

HRID 2046186 reaction equation
CCN(S(F)(F)[F:7])CC.O[CH:11]1[N:16]2[N:17]=[C:18]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=[C:15]2[C:14](=[O:28])[NH:13][CH2:12]1>C(Cl)Cl>[F:7][CH:11]1[N:16]2[N:17]=[C:18]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=[C:15]2[C:14](=[O:28])[NH:13][CH2:12]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67973603(rac)-7-hydroxy-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one

Product 1

HCID 67973614(rac)-7-fluoro-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-oneYield 102.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DAST (0.035 mL, 0.29 mmol) was added to a solution of (rac)-7-hydroxy-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (50 mg, 0.19 mmol) in DCM (0.5 mL) at −10° C. The mixture was stirred at room temperature for 15 minutes. Then quenched with a 1N solution of HCl and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield (rac)-7-fluoro-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (51 mg, quantitative) as light brown solid that was used without further purification.

Workup

  1. customThen quenched with a 1N solution of HCl
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-9b5bb7b95acb4274abb85477336f243d
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

Loading…